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. 2022 Apr 7;78(Pt 5):485-489.
doi: 10.1107/S2056989022003723. eCollection 2022 May 1.

Crystal structure of 4-bromo- N-(propyl-carbamo-yl)benzene-sulfonamide

Mustafa Bookwala  1 , Saloni Patel  1 , Patrick T Flaherty  1 , Peter L D Wildfong  1
Affiliations

Crystal structure of 4-bromo- N-(propyl-carbamo-yl)benzene-sulfonamide

Mustafa Bookwala et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The title compound, C10H13BrN2O3S, 1, contains a sulfonyl urea moiety, which possesses potential therapeutic functions (e.g., anti-diabetic and herbicidal). The geometry of 1 is similar to its closely related analogues, chlorpropamide and tolbutamide. This compound crystallizes in the monoclinic space group C2/c, having one mol-ecule in its asymmetric unit. The crystal structure of 1, recorded at 296 K, shows inter-molecular N-H⋯O and C-H⋯O-type infinite hydrogen-bonded chains involving the sulfonyl urea moiety. Hirshfeld surface analysis and the two-dimensional fingerprint plots confirmed hydrogen bonding as the dominant feature in the crystal packing.

Keywords: bromo­propamide; crystal structure; single-crystal XRD; structural analogue.

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Figures

Figure 1
Figure 1
The mol­ecular structure of 4-bromo-N-(propyl­carbamo­yl)benzene­sulfonamide with atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Figure 2
Infinite hydrogen-bonding involving the sulfonyl urea moiety in 4-bromo-N-(propyl­carbamo­yl)benzene­sulfonamide. Hydrogen bonding between N1—H1⋯O2, N2—H2⋯O2, N2—H2⋯O3, and C10—H10C⋯O1 is shown as green dotted lines. Displacement ellipsoids are drawn at the 30% probability level. Only H atoms involved in hydrogen bonding are shown.
Figure 3
Figure 3
The crystal packing in 4-bromo-N-propyl­carbamo­yl)benzene­sulfonamide viewed along the b axis. Anti­parallel stacking of the bromo­phenyl has a centroid-to-centroid distance of 4.213 Å. Displacement ellipsoids are drawn at the 30% probability level. H atoms are not shown for clarity.
Figure 4
Figure 4
Hirshfeld surface of 4-bromo-N-(propyl­carbamo­yl)benzene­sulfonamide mapped over d norm, displays close contacts in the crystal. The non-covalent inter­actions indicated by the red spots are labeled.
Figure 5
Figure 5
The two-dimensional fingerprint plots of 4-bromo-N-(propyl­carbamo­yl)benzene­sulfonamide with their relative contribution to the Hirshfeld surface. The units of d i and d e are Å.
Figure 6
Figure 6
Reaction scheme for the synthesis of 4-bromo-N-(propyl­carbamo­yl)benzene­sulfonamide.
See this image and copyright information in PMC

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